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Oak Bluffs Summer Rentals

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    Travellers to Oak Bluffs are booking June dates now. Secure your holiday home today, and have the perfect trip.
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    4 Bedrooms, Sleeps 8Quick View
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    Spectacular water view in desirable East Chop neighborhood. This 4 bedroom, 3 bath home is just 1.5 miles from Oak Bluffs Center and Beach. There is a yard with multiple decks and waterviews. Features include central air and wifi internet. Beautifully decorated. Amenities and Features include......
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6Quick View
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    Come experience the magic of the Vineyard in our island home. Modernized in 2011, this charming residence is clean, cozy and boasts new furniture and decor. Amenities include 3 TV’s, cable television, Wi-fi, DVD, telephone, I-home, and Keurig Coffee maker. The property has a private yard, sundeck,...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 10Quick View
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    This magnificent 1920’s East Chop cottage has been extensively redesigned, refurbished and expanded to allow friends and families to enjoy luxury accommodations along with rare double views of both Nantucket Sound and neighboring Crystal Lake. Complemented with a huge wrap around deck and a covered...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, Sleeps 12Quick View
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    About this property
    Just a block from the East Chop Bluffs on a sleepy side street in a quiet wooded setting. There are 2 SEPERATE LIVING ROOMS!! Large bright kitchen that accesses a separate dining room, inviting screen porch with dining and sitting areas, and sunny rear deck with lots of backyard privacy. Ocean...
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    Oak Bluffs, Martha's Vineyard 02257
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, Sleeps 7Quick View
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    About this property
    Air conditioning has been added for the 2017 season! Waterview Farm is a private association with wonderful meadow and water views. It is adjacent to Farm Neck Golf and Tennis Club, which is open the public. There is access to Sengekontacket Pond to launch canoes and kayaks from the private...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, Sleeps 8Quick View
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    This unique and elegant four bedroom beach cottage is situated on the north shore of Martha's Vineyard. For your relaxation, there is a large porch/patio leading out to the beach affording magnificent views. Additional views from the tastefully decorated living area, bedrooms areas, make this a...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 8Quick View
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    • Balcony
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    About this property
    New Renovated, 1870 historic "Campground" cottage centrally located in Oak Bluffs, The cottage has 4 bedrooms (all located on the second floor) - 1 queen, 2 double beds and 2 twins beds. The front bedroom has its own balcony with water views. Cottage sleeps 8. the first floor includes a newly...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    This charming Cape style Oak house residence is situated on a wooded lot near bike path and just a short ride to town center and ferry. This home features an open design with a bright kitchen/dining/living area with hardwood floors, den and full bath on the first floor. Sliders in the dining area...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    Relax in optimal comfort at this Oak Bluffs home. It's got four bedrooms and lots of space for an ideal family vacation! You're in the heart of Oak Bluffs, within walking distance of the harbor and lovely waterfront. You can hop off the ferry to Martha's Vineyard and be here in no time. This...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    6 Bedrooms, Sleeps 10Quick View
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    About this property
    Come and enjoy this beautiful waterfront home on East Chop! The first floor has a wonderful front seasonal porch with views of the Vineyard Sound. There is a large dining table and room to relax and take in the view. There is also a living room that leads into the kitchen on the 1st floor. The...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    Walk to the beach! Walk to restaurants and shopping! Walk the kids to the arcade, Flying Horses Carousel, and lots of ice cream! Stay at a beautiful and bright home in the Historic Copeland District in Oak Bluffs. This 1928 home is mere minutes from dining and shopping on Circuit Avenue and the...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beautiful four bedroom home within walking distance to the Oak Bluffs harbor and town. This home has a nice size first floor living room and separate eat in kitchen. The first floor also has a full bathroom with tub and shower. The second floor has four bedrooms and one full size bathroom. The...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, Sleeps 6Quick View
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    This grand Victorian jewel on Ocean Park has been completely renovated and transformed into a beautiful vacation home. Enjoy water and park views from inside this elegant home, the expansive wraparound porch and the second floor balcony. This beautifully restored Victorian home is a rare find...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    Nestled in a private location on Crystal Lake which abounds with bird life, this is a delightful, vintage 1950's home with modern conveniences and comfortable furnishings. Its rambling single story layout is spacious and conducive to relaxed living. It is very well maintained and well equipped. The...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, Sleeps 12Quick View
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    About this property
    It's all about the stellar location of this five-bedroom Oak Bluffs getaway, a wonderfully renovated Victorian home with a front porch and deck, four bikes to help you explore Martha's Vineyard, and an enclosed yard that is ideal for kids. This two-level house sits just half a mile from the...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    This wonderful family vacation home features lovely waterviews across Crystal lake. The peaceful location and large yard provide the perfect venue for extended families with children. Relax on the expansive deck, enjoy the views from the 4 person glider swing as seen in the photos Families will...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    Quietly nestled on quiet street just on the outskirts of town, this brightly lit home features a mix of coastal details and traditionally styled upscale furnishings for your comfort. The interior has open floor plan that flow nicely to outdoor living spaces including a screened porch and brick...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    • Balcony
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    • Private Outdoor Pool (Heated)
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    About this property
    New to the 2015 Summer Season! This spacious waterfront home offers 4-bedrooms en-suite, with family, game and fitness rooms...and yes, a pool. The peaceful setting is centrally located, yet close to the village center for easy access to shops, restaurants and more. The home is tastefully...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    6 Bedrooms, Sleeps 14Quick View
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    • DVD Player
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    • Porch
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    Pet friendly
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    About this property
    Historic summer "cottage" with 7 bedrooms, sleeping porches, a deck overlooking the water, a private dock on Harthaven Harbor, and immediate access to the ocean. The rustic home is a perfect gathering spot for family and friends. It has a large living room with a huge stone fireplace, an eat-in...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 14
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    4 Bedrooms, Sleeps 7Quick View
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    • Central Heating
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    About this property
    This 4 bedroom home with skylights, 52 inch Tv, computer, internet, printer, fax, is your home away from home. 1 mile from town 1.5 mile from beach and 7 miles from airport is ideal location. 2 SETS OF GOLF CLUBS AND 4 TENNIS RACQUETS FOR YOUR USE, 3 CABLE TV'S, MASTER BATH HAS WHIRLPOOL TUB...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, Sleeps 4Quick View
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    About this property
    Soak in one of the loveliest sunset views on Martha's Vineyard when you escape to this two-bedroom Oak Bluffs cottage, where you'll enjoy a short walk to the ferries and a private deck with panoramic views of Lagoon Pond, Brush Pond, Vineyard Sound, and Vineyard Haven. This single-level cottage...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, Sleeps 8Quick View
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    About this property
    This gorgeous, contemporary air-conditioned private home is perfect for your luxurious vacation on the island. It is 2700 sq ft of well laid-out space and sits on 1.4 acres of land in a private wooded area, centrally located, only minutes from downtown Oak Bluffs and beautiful beaches. The...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 4Quick View
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    Stay in this peaceful, well-maintained home with a large wrap-around porch, a deck, and in close proximity to the ocean for your next unforgettable New England vacation. Come with a small group of friends, bring your own small family, or get away with another couple and rest assured that you'll...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, Sleeps 10Quick View
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    About this property
    A fully renovated four bedroom home with 3 1/2 baths, family room, landscaped lot and a private beach and dock. Dock can accommodate up to a 25 foot motor boat, located on The Lagoon and is accessible to Vineyard Sound. Family room has cable TV, deck, fully equipped kitchen, and a 2 person kayak...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, Sleeps 6Quick View
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    About this property
    Modern two bedrooms, one bath cottage situated at the end of a quiet street. This cozy cottage is Oak Bluffs center and the town beaches. The home has recently been renovated with new comfortable furnishings including linens and mini spit air located about one mile to shops, restaurants in...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    Beautiful and spacious 3 bedroom in Oak Bluffs, Martha's Vineyard. Sunny, open and airy Cape. Walking distance to town, gingerbread cottages, library, and playground. Close to beach, golf course, and great fishing spots. There is a pack and play in the upstairs bedroom for a baby to sleep or nap...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick View
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    About this property
    Note: Interior photos are of a unit with same floor plan, see details below for description of decor of unit not shown in these photos. Waterfront Seaview Condo # 205 is a corner unit and is being all newly painted and furnished for Summer 2017. Photos of completed unit will be available late April...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, Sleeps 5Quick View
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    For your next getaway, escape to this fabulous 3-bedroom, 2-bathroom Oak Bluffs vacation rental condo that comfortably sleeps 5. Steps away from the beach, this condo offers beautiful ocean views and comfortable accommodations. Whether you’re seeking time on the beach or an art-inspired getaway,...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    5 Bedrooms, Sleeps 22Quick View
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    • Hot Tub
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Smoking allowed
    About this property
    This upscale, newly renovated, 4 bedroom home in a quiet neighborhood in Oak Bluffs. You are 2.5 miles from the town center and Inkwell and State beautiful public beaches. This home boasts a large unground back yard pool and hot tub on the mahogany deck. Large outdoor shower. Grill and fire pit...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 22
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    5 Bedrooms, Sleeps 13Quick View
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    About this property
    Newly renovated 5 bedroom home just a mile and a half from the center of Oak Bluffs. New hard wood floors throughout as well as updated furnishings and decor. Dining area is extended by a nice sized sunny deck for outdoor dining. Perfect for a large family vacation. Additional amenities include:...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    4 Bedrooms, Sleeps 8Quick View
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    • Terrace
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    About this property
    This classic Oak Bluffs home is filled with antiques and has views of the pier from the front porch. It's the perfect home for families wanting a relaxing getaway. This historic cottage is only five minutes away from Ink Well Beach and the Steamship Authority Dock, and is just a half mile from the...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    8 Bedrooms, Sleeps 20Quick View
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    About this property
    Amazing five acre property! 6 BR main house w/ pool + a 2 BR carriage house! Our amazing property is perfect for everything from a memorable family vacation to a serene retreat. You and your guests will begin to enjoy the feeling of privacy the minute you arrive as you drive down the long tree...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 20
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    4 Bedrooms, Sleeps 8Quick View
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    • Grill
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    About this property
    Historic harborfront home with private dock has been completely renovated and newly furnished, beautifully appointed throughout to reflect summer living on the Vineyard. The large living and dining areas open onto the expansive and comfortably furnished porch, overlooking picturesque Oak Bluffs...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Wi-Fi
    • Waterfront
    • Grill
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with waterviews over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in dining overlooking the pool. The...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 12Quick View
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    • Grill
    • Wi-Fi
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to "Shangrila" A beautiful townhouse condominium end unit with magnificient views. Located midway between Oak Bluffs and Edgartown. You can enjoy the beautiful pool or one of the close local beaches. You will want to sit and enjoy the water views on the deck. The townhouse has a great...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, Sleeps 9Quick View
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    • Wi-Fi
    • Waterfront
    • Ocean Views
    • Air Conditioning
    • Parking
    • Washer
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious gingerbread directly across from Union Chapel. Sit and watch the action roll by from the comfort of large front porch or enjoy the quiet and private yard/patio on the side of the house. Even though there are 3 parking spots on the premises the location affords you the luxury to easily walk...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, Sleeps 6Quick View
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    • Internet Access
    • Parking
    • Satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tucked away among the shade trees on Martha's Vineyard, this delightful cabin in the woods is ideal for your next family vacation or getaway with a few close friends. This three-bedroom rental is located less than a mile from the top-ranked, semi-private Farm Neck Golf Club as well as the Trade...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and enjoy this three level contemporary home with a beautiful landscaped yard. There is a wonderful deck off the kitchen with outdoor dining and seating area. the first floor offers and open kitchen, dining and TV/living room area. The is a second sitting room on this floor as well. The...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    3 Bedrooms, Sleeps 12Quick View
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    • Satellite TV
    • Patio
    • Air Conditioning
    • Ocean Views
    • DVD Player
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is our beautiful home on Martha's Vineyard we call Shangi-La! Spectacular setting with a great peaceful view overlooking Sengekontacket Pond with the Ocean beyond. The property features a shared Pool, Tennis Courts, and a Dock. Our house is conveniently located midway between the Oak Bluffs &...
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    Oak Bluffs, Martha's Vineyard 02539
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, Sleeps 4Quick View
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    • Internet Access
    • Washer
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great Getaway Cottage with a short walk to Circuit Ave, the harbor, and the Lagoon .A back yard w/ picnic table, BBQ grill. About a mile walk or bike ride to Town. The house has hardwood and fir floors throughout and also has air conditioning. This is a great "get away cottage" for a small family...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 4Quick View
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    • Parking
    • Private Garden
    • Patio
    • Grill
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully Appointed Renovated 2 Bedroom Cottage close to Lagoon Heights Beach. Bedrooms have cozy Queen Beds with Ceiling Fans. 1 Bathroom with Large Soaking Tub,and Outside Shower with Hot Water. Breezy , Quiet , Large Yard Parking For 2 Cars Open Living Dining Kitchen Area. Outside Patio...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, Sleeps 7Quick View
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    • Patio
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This adorable Gingerbread cottage is located only a block to town and a couple of blocks to the beach. You can enjoy morning coffee on the covered wrap around porch that leads into a cute sitting room with a TV and another small sitting area off of the front room. There is also a nice size dining...
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    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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